3 Key West Fall Festivals & Events You Don’t Want To Miss!

Are you searching for the best fall festivals and events in Key West from September through November?  We’ve got three celebrations you’ll want to add to your travel bucket list.  It all starts Labor Day Weekend with Key West Brewfest; in October, we celebrate ten days of creative costuming, parades, and themed parties with Fantasy Fest. In November, we welcome the Offshore World Championship Boat Races. 

Southernmost Beach Resort and sister property, The Marker Key West Harbor Resort, are proud sponsors of Key West Brewfest, Fantasy Fest, and the Race World Offshore World Championship.   

Key West Brewfest, September 1-5

Key West BrewFest has become the largest event by Key West Sunrise Rotary that raises funds to provide yearly educational scholarships to local students and charitable donations to other non-profit organizations. The multi-day festival includes beer pairing dinners, pool parties, and other activities around town, culminating with the signature tasting event on the beach.

Southernmost Beach Resort, a proud sponsor of Brewfest, has been involved since day one, and we can’t wait to share this year’s schedule. 

WHAT’S HAPPENING AT OUR RESORTS DURING BREWFEST

Thursday, September 1st

Key West Brewfest afternoon kickoff takes place at The Marker Key West Harbor Resort!

1 pm – 4 pm The Marker Key West Harbor Resort – Pool Party, Sponsored by South Beach Brewing

Friday, September 2nd

Afternoon Pool Party and 5 Course Beer Pairing Dinner 

1 pm – 4 pm – Southernmost Beach Resort: Pineapple Pool Party, Sponsored by Islamorada Brewing Company

7 pm – Southernmost Beach Resort – BrewFest 5-Course Beer Pairing Dinner with FL Keys Brewing – See Menu

Saturday, September 3rd

BrewFest Signature Tasting Festival at South Beach

3 pm – 5 pm – VIP Hours (Tickets $100)

5 pm – 8 pm – General Admission (Tickets $40)

Buy Tickets – Key West Brewfest Signature Tasting Event

Sunday, September 4th

6 pm – 9 pm – Glass Cats Live on the beach!  FREE show at Southernmost Beach Resort. Get your FREE tickets.

Learn more about the Key West Brewfest.

Fantasy Fest, October 21-30

2022 Theme: Cult Classics & Cartoon Chaos

Photo Credit: Mandi Ilene Schiff via Fantasy Fest

Are you ready for Fantasy Fest 2022: “Cult Classics and Cartoon Chaos,” ten days of fun-filled costuming, parades, libations, and excitement that takes place October 21-30?

There will be costume competitions, themed parties, pool parties, a pet parade, a masquerade march, street fairs, a grand parade that stars marching groups, island-style bands and lavish floats. The only way you’ll look out of place is if you don’t dress up, so start planning now. 

If you get stuck and can’t come up with creative costume ideas, view the Fantasy Fest photo gallery for inspiration. 

What’s happening at our resorts during Fantasy Fest

Southernmost Beach Resort and our sister property, The Marker Key West Harbor Resort, are sponsors of Fantasy Fest 2022.  Here’s what’s happening at our properties:

THE HEAVY PETS, LIVE ON THE BEACH AT SOUTHERNMOST BEACH RESORT

Thursday, October 27th at 3 pm

The Heavy Pets are a funked-up rock and roll band from South Florida. Called “a living, breathing force of nature” by Relix magazine, they are known for their songcraft and powerhouse live performances. The band has been a mainstay on the national touring circuit for over a decade and released its fourth full-length studio album Strawberry Mansion in February 2018.  FREE Concert! Reserve your space here.

RED ELVISES POOL PARTY AT THE MARKER KEY WEST HARBOR RESORT

Friday, October 28th, 4 pm 

Get your swimsuit and come out to party with Red Elvises! This band has produced 12 studio albums, two live albums, a live concert DVD, and a Greatest Hits compilation. Some of their most notable film contributions include music and or performances in “Six String Samurai,” “Mail Order Bride,” “Armageddon,” “Skippy,” “Melrose Place,” “Fastlane,” “Penn and Teller’s Sin City Extravaganza,” “VH-1 Behind the Music”, and “MTV. No matter where they perform, Igor & Red Elvises always bring the party with them.

FREE Event! Reserve your space here. 

GLASS CATS LIVE ON THE BEACH AT SOUTHERNMOST BEACH RESORT

Saturday, October 29th, 3-6 pm

The ultimate beach & BBQ Rock & Roll party! Glass Cats has been playing their experimental jam-based, funky soul-filled grooves around town for the past couple of months, and they’re AMAZING! The four-piece band consists of Myles Mancuso on guitar and vocals, Mark King on bass and vocals, Michael Wingate on keys and vocals, and Evan Valentine on drums and vocals.

FREE Concert! Reserve your space here.

HANGOVER POOL PARTY AT SOMO’S PINEAPPLE POOL

Sunday, October 30th, 1-4 pm at Southernmost Beach Resort 

We’ll have plenty of food and drink specials, a live DJ spinning all your favorites, and free Booze Bandages for the first 50 guests to bring you back to life!

FREE Event! Reserve your space here.

REGGAE REHAB POOL PARTY AT THE MARKER KEY WEST HARBOR RESORT  with REGGAE LOU & THE KIND BUDZ

Sunday, October 30th, 2-5 pm 

Are you feeling hungover after your long week of debauchery? Captain Morgan, Ketel One Botanicals, and Booze Bandage to the rescue! We’ll have plenty of food and drink specials, live music by Reggae Lou, and free Booze Bandages for the first 50 guests to bring you back to life!  See you at The Marker Key West Harbor Resort, 200 William St. 2-5 pm. 

FREE Event! Reserve your space here.

Learn more about Fantasy Fest 2022 Cult Classics and Cartoon Chaos.  

Race World Offshore World Championship

November 6-13

Race World Offshore is excited to bring teams and fans to Key West for an amazing Offshore World Championship with the world’s best offshore race teams in attendance. Racing teams and fans will gather for an exciting Offshore World Championship experience. 

Southernmost Beach Resort is an Executive Sponsor, and The Marker Key West Harbor Resort is a Conch Sponsor of the Race Offshore World Championship.  Take a look at the events taking place during race week.  

• There are 3 Days of racing Wednesday, Friday & Sunday 
• Race Village, located at Truman Waterfront Park, is open 9 – 5
• Sunday prior, World’s Fastest Boat Parade on Duval 4:00 pm
• Friday the famous Duval & Greene Street Block Party with your favorite Race Boats
• Saturday 3rd Annual Build-A-Boat Contest with Community & Race Teams
• View the 2022 World Championships Event Schedule 

Learn more about the Race World Offshore World Championship.   

Stay up to date on all the fall fest happenings.  Check out the Key West Brewfest, Fantasy Fest and Race World Offshore World Championship event schedules, subscribe to Southernmost Beach Resort Events on Facebook, and share your favorite memories with us!  #somolife